An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines

Abstract An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally friendly cerium trichloride as catal...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-12, Vol.49 (24), p.5387-5395
Main Authors: Cimarelli, Cristina, Bordi, Samuele, Piermattei, Pamela, Pellei, Maura, Del Bello, Fabio, Marcantoni, Enrico
Format: Article
Language:English
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Summary:Abstract An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally friendly cerium trichloride as catalyst and allows to obtain either the anti - or the syn -isomer of the final tetrahydroquinoline with good selectivity, by performing the reaction in solvent or solventless conditions. The scope of the reaction is expanded to the one-pot synthesis of N -alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1589104